Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
  • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
  • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
  • C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound

Definitions

• the present invention relates to new aromatic polycondensates containing carboxamide and sulphonamide groups.
• the present invention relates to polycarboxamide-sulphonamides which are infusible, and are soluble in organic solvents at high concentrations without it being necessary to add inorganic salts.
• These polymers consist essentially of recurring units of the formula:
• each of the Ar radicals which may be identical or different, represents a divalent aromatic radical containing one or more benzene rings
• n is 0 or an integer equal to or greater than 1.
• the arrow above the --SO 2 NH-- groups signifies that each of these groups can be reversed to give --NHSO 2 -- groups.
• the present invention relates, in particular, to the polymers in which n is equal to 0 or to 1, that is to say polymers in which the ratio between the number of carboxamide units and sulphonamide units is 2:1 or 1:1.
• aromatic diacids of formula HOOC -- Ar 1 -- COOH which can be used to prepare these products can be, for example, terephthalic acid, isophthalic acid, a dicarboxydiphenyl acid, a dicarboxynaphthalene, a dicarboxydiphenylmethane, a dicarboxydiphenyl ether or a dicarboxydiphenyl thioether.
• the diamines which can be used have the formula:
• amines can be synthesised by known methods, for example by reacting an aromatic diamine with an amino-arylsulphonic acid or its chloride according to the equation:
• Polycondensation of the diacid or of its chloride with the diamines can be carried out in accordance with the usual methods for the preparation of polyamides, for example in solution in a polar organic solvent such as dimethylacetamide, hexamethylphosphotriamide or N-methylpyrrolidine.
• the reaction can be carried out at ambient temperature but it can be accelerated by heating.
• Isolation of the polymer can be carried out by pouring the reaction mixture into water, preferably with vigorous stirring; the polymer usually precipitates in the form of granules from which all traces of acidity can be removed by washing with water.
• the polymers thus obtained are infusible products which are resistant to temperatures as high as 350°-450°C; they can be dissolved, at concentrations which can be as much as 40 percent, in organic solvents such as aliphatic or cyclic amides like dimethylformamide, dimethylacetamide, N-methylpyrrolidone and mixtures thereof.
• Their solutions are transparent and can be cast or extruded in order to prepare infusible films and fibres which are resistant to heat and possess good mechanical properties, in particular high tensile strength and a high modulus.
• the polymer is then in the form of infusible whitish granules which are soluble at ambient temperature in various solvents such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone and hexamethylphosphotriamide.
• solvents such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone and hexamethylphosphotriamide.
• a 20 percent strength solution in dimethylacetamide has a viscosity of 350 poises.
• This polymer is infusible and resists temperatures of 300°-350°C., in air or in an inert atmosphere, without degradation.
• a solution in dimethylacetamide with a solids content of 15 percent is suitable for casting films.
• Example 5 is prepared, which has an inherent viscosity, determined as in Example 5, of 0.66 dl/g., and which is infusible and resists temperatures of 300°-350°C. without degradation.
• This solution is then concentrated to 32 percent by evaporation at 110°C./160 mm.Hg, and is then passed through a spinneret heated at 114°C.
• the fibre produced passes through a column heated at 180°C., whilst being pulled at the rate of 25 m/minute, and is then taken up continuously in water and dried on a roller at 75°C. It is then partially stretched (ratio 2:1) before being stretched finally at a ratio of 1.6:1 above a plate heated at 350°C.
• the yarns thus produced have the following properties:

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Polyamides (AREA)
• Artificial Filaments (AREA)

Applications Claiming Priority (2)

Publications (1)

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Family Applications (1)

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Cited By (4)

Citations (2)

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• 1972
  • 1972-09-13 FR FR7232426A patent/FR2198973B1/fr not_active Expired
• 1973
  • 1973-09-04 NL NL7312211A patent/NL7312211A/xx not_active Application Discontinuation
  • 1973-09-10 JP JP48101264A patent/JPS4967996A/ja active Pending
  • 1973-09-10 US US05/395,435 patent/US3931119A/en not_active Expired - Lifetime
  • 1973-09-11 BR BR7022/73A patent/BR7307022D0/pt unknown
  • 1973-09-12 BE BE135594A patent/BE804782A/xx unknown
  • 1973-09-12 CA CA181,007A patent/CA1012292A/fr not_active Expired
  • 1973-09-12 GB GB4290773A patent/GB1442136A/en not_active Expired
  • 1973-09-12 CH CH1309573A patent/CH574463A5/xx not_active IP Right Cessation
  • 1973-09-13 IT IT28890/73A patent/IT998602B/it active
  • 1973-09-13 DE DE19732346227 patent/DE2346227A1/de active Pending

Patent Citations (2)

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